Deals on vacations and trips to Canaan

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Canaan flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Windham NY Escape

Windham NY Escape

3 out of 5
Price was $890, price is now $797 per person
$797
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Luggage storage is available at this cabin. Take advantage of the free self parking.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $6,130, price is now $4,762 per person
$4,762
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $6,142, price is now $4,775 per person
$4,775
per person
Oct 23 - Oct 26
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,378, price is now $1,214 per person
$1,214
per person
Oct 8 - Oct 11
found 3 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $3,365, price is now $3,061 per person
$3,061
per person
Oct 8 - Oct 11
found 3 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Hudson (HCC)
This chalet features a hot tub and a sauna. Free self parking and a terrace are also offered on site.

Top Canaan hotels deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$208 nightly
The price is $232 total per night
$232 total
Sep 8 - Sep 9
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
$93 nightly
The price is $103 total per night
$103 total
Sep 15 - Sep 16
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
190 Meadow Street South Lee MA
$135 nightly
The price is $150 total per night
$150 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
Free Cancellation
$110 nightly
The price is $122 total per night
$122 total
Sep 15 - Sep 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. A restaurant, a 24-hour front desk, and express check-out are also provided.
Breakfast included
Free WiFi
Little Cat Lodge

Little Cat Lodge

2 out of 5
37 Catamount Rd Copake Falls NY
$245 nightly
The price is $274 total per night
$274 total
Aug 27 - Aug 28
Total with taxes and fees
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a garden are also on offer.
Pool
Breakfast included
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
$125 nightly
The price is $140 total per night
$140 total
Sep 1 - Sep 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and express check-in are also on offer.
Pet friendly
Parking included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Canaan attractions

North Canaan Town Hall

North Canaan Town Hall is just one of the places to see in North Canaan, so why not enjoy the other things to explore during your travels?
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Frequently asked questions

How much are vacation packages to Canaan?
Packages, which include flights and hotels in Canaan, start from as low as $797. Make your travel fantasies come to life and secure your dream vacation with Travelocity today.
How long should my Canaan vacation be?
Many travelers spend about 3 nights in Canaan, but it's entirely up to you. If you hope to discover all the wonderful things this destination has waiting for you, why not hang around for a few extra nights?
Where can I get the best vacation package deals for Canaan?
No matter how you like to travel, Travelocity can help you get your hands on an unbeatable Canaan package deal. All you need to do is pick and choose between our 400 air carriers and 1,000,000 properties worldwide.
Why should I purchase my Canaan vacation package with Travelocity?
Whether you're in search of the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to search through countless websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7.
Can I save on my Canaan car rental if I bundle it with my hotel or flight?
With a Canaan vacation package, you can bundle your car, flight and hotel bookings and save tons. If you want to uncover the best of this fantastic location, why not head to Times Square? This famous sight is 95 mi from Canaan. With your own wheels, you'll be there before you know it.
Which airport is best for Canaan?
Many fly into Bradley Intl. Airport (BDL), 35 mi east of downtown Canaan. Others prefer Albany Intl. Airport (ALB) (55 mi away from central Canaan) or Tweed - New Haven Regional Airport (HVN) (55 mi away from central Canaan).
Where should I stay when visiting Canaan?
Many people opt to check in to the Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.. It's an excellent base for your Canaan vacation.

Photos of local treasures

Browse Canaan vacation photos for more inspiration

A red bridge over a river with snow patches and dry grass.
A stone tower surrounded by lush greenery and trees.
A waterfall cascading over rocks, a small building, and a forested hillside.

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